Glycidyl derivatives are essential intermediates used for the preparation of medicines, agricultural articles, bio-products and fine-chemicals [Chemical Reviews, Vol. 91, 437 (1991)]. Generally, the glycidyl derivatives are prepared by derivatizing glycidol in a presence of a base and a solvent. The yield and optical purity of the glycidyl derivatives are largely dependent upon reaction conditions.
U.S. Pat. Nos. 4,946,974 and 5,252,759, and Japanese unexamined patent publication No. 6-179663 disclose a process for producing glycidyl derivatives, comprising reacting glycidol with a substrate in a presence of a tertiary amine, in an organic solvent or in a two phase solvent consisting of an organic solvent and water. Due to the instability of the glycidol, the process produces various side products. In addition, the reaction rate is so slow that the process is not economical.
In order to overcome the disadvantages, Japanese unexamined patent publication No. 7-165743 discloses a process for the preparation of glycidyl derivatives, comprising treating 3-chloro-1,2-propanediol with an alkali metal carbonate in an organic solvent and without isolation of the resulting glycidyl, subjecting it to reaction with p-toluenesulfonyl chloride, a tertiary amine and 4-(dimethylamino)pyridine to produce glycidyl tosylate. As indicated in U.S. Pat. No. 5,965,753 filed by the same applicant, however, the process suffers from disadvantages that the reaction rate is low and various side products are produced, which deteriorates chemical purities and optical purities of the desired products.
As an improvement of the process of the Japanese unexamined patent publication No. 7-165743, U.S. Pat. No. 5,965,753 discloses a process for the preparation of a glycidylsulfonate derivative in one reaction vessel which is characterized in that reacting 3-chloro-1,2-propanediol in an aqueous solvent in a presence of a hydroxide salt or a carbonate salt, and without isolating the resulting glycidol, subjecting it to reaction with a sulfonyl halide in a two phase solvent consisting of an organic solvent and water in the presence of at least one inorganic base selected from the group consisting of a hydroxide salt and a carbonate salt, and a tertiary amine or a pyridine derivative. However, the process has very narrow applicability, for example, to the preparation of a chiral glycidyl sulfonate from sulfonyl chloride which is stable in water. The process can not be applicable to acid halides (or acyl halide) or acid anhydrides which are sensitive to the presence of water. Furthermore, as suggested in German patent No. 1,226,554 and U.S. Pat. No. 2,248,635, the carbonate salt is generally used in an organic solvent, and a hydroxide salt in an aqueous solvent.